Michael Holloway
Entertainment

Big Trucks and Maifest Offer Something For All Ages

Have you ever wondered what it feels like to issue a parking ticket? Now’s your chance.

By - May 14th, 2026 04:33 pm
Aubrey Jannene prepares to issue parking tickets at Big Truck Day 2022. Photo by Jeramey Jannene.

Aubrey Jannene prepares to issue parking tickets at Big Truck Day 2022. Photo by Jeramey Jannene.

It’s looking to be a warm but wet weekend in Milwaukee, but don’t let the rain keep you in – there are plenty of events to check out around the city this weekend.

Big Truck Day will bring Milwaukee’s largest vehicles to Red Arrow Park, giving families the opportunity to climb into the driver’s seat. Maifest, the Midwest’s largest gluten-free festival, is celebrating its fifth year, and Festival of Flowers will bring flower-themed art and pop-up markets to the Milwaukee Public Market

May 14-17: Milwaukee Auto Show

Test drive your dream car at the Milwaukee Auto Show, where over 25 brands will bring their latest innovations and newest models to the Wisconsin State Fair Exposition Center. Guests can chat with industry professionals and compare vehicles side by side to discover which model is best for you. On Saturday and Sunday, check out Milwaukee Motorfest, where musclecars, custom builds, classic cars and more will be in the spotlight. The Milwaukee Auto Show will run from noon to 9 p.m. on Thursday, 10 a.m. to 9 p.m. on Friday, 10 a.m. to 9 p.m. on Saturday and 10 a.m. to 6 p.m. on Sunday. For more information, visit the Milwaukee Auto Show website

May 15: MAM After Dark: The Blue Room

The Milwaukee Art Museum will transform into a surreal jazz lounge as part of the Milwaukee After Dark event series. After regular hours, the museum will transform into The Blue Room, an atmospheric jazz setting inspired by Gertrude Abercrombie: The Whole World Is a Mystery. Guests can enjoy live jazz from groups such as The Wisconsin Conservatory of Jazz Trio, play life-size checkers, have their portraits painted and more. MAM After Dark will run from 7 p.m. to 10:30 p.m. For more information, visit the Milwaukee Art Museum’s website

May 16: Festival of Flowers

The Milwaukee Public Market is hosting the second annual Festival of Flowers, a free celebration that transforms the Riverwalk Commons into a colorful spring experience. The event will feature a flower display courtesy of the Botanical Collective as well as a pop-up flower market where local vendors such as Wood and Floral and Mobile Mini Trucks will be selling flower-themed art and more. Festival of Flowers will also feature live music and seasonal food and drinks available for purchase. The event will run from 11 a.m. to 3 p.m. For more information, visit the Milwaukee Public Market’s website

May 16: Bravery in Bloom

Courage+ is putting on Bravery in Bloom, a queer arts festival that aims to bring creativity and expression to Milwaukee’s south side. The inaugural event will feature LGBTQIA+ artists and makers set up along the stretch of S. 21st St. between National Ave. and Pierce St. Guests can experience live performances including a drag show, and watch artist Jeremy Novy lead the creation of a large-scale butterfly mural. The free event will also feature community resource booths and family-friendly art activities. Bravery in Bloom will run from noon to 6 p.m.  

May 16: Big Truck Day

Celebrate National Public Works Week with the biggest vehicles the city has in its fleet. This family-friendly event will see the city’s workhorse big rigs parked around Red Arrow Park, allowing families to explore various trucks and meet the friendly faces who operate them. The event will feature dozens of vehicles and the first 1000 children who attend the event will receive kid-sized construction hats and goodie bags. The event is free to attend. For more information, visit the Milwaukee Downtown website

May 18: Maifest

The midwest’s largest gluten-free festival is celebrating its fifth anniversary! Lakefront Brewery’s Maifest will bring live music, street performances, a rummage sale and more to the brewery’s outdoor area. For the first time, Maifest will not only take place on the brewery’s patio, but it will spill out onto the parking lot as well as a section of Commerce St. The brewery will be releasing a Gluten-Free Cherry & Sakura Sparkling Mead aged in Wollersheim Brandy Barrels as well as a new variety of the brewery’s iconic gluten-free beer New Grist. Maifest is free to attend and will run from 10 a.m. to 3 p.m.

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